New acrolein condensation product



Patented Feb. 16, 1932 UNITED STATES PATENT OFFICE WALTER morr, OFELBE BIELD, NEAR COLOGNE-Or-THE-RH'INE, GERMANY, ABSIGNOB TO I. G. IABBENINDUSTBIE AKTIENGEBELLSCHAIT, OI FRANKFORT-ON-THE-MIH,

GERMANY HEW AGBOLEIN CONDENSATION PRODUCT Ho Drawing. Application filed larch 8, 1928, Serial ll'o. 92,952, and in Germany August 6, 1925.

The present invention concerns the manufacture of technically valuable compounds by the condensation of 41-, fl-substituted acrolein with aromatic bases, the products being obtained in good yield in spite of the tendency of the a-SllbStitlltiOIl to hinder the reaction. The new roducts result by the simle interaction 0' the components and may e designated as acrolein Schifis bases. They are intended to find application as accelerators in the vulcanization of rubber and as intermediate compounds for the manufacture of technically important substances. The new compounds are also characterized by additional valuable properties by virtue of which they may be employed to protect rubber goods against deterioration due to age. The new products having probably the following general formula wherein R and R, stand for alkyl groups and R, stands for an aromatic nucleus are generally oils being soluble with difliculty in water and being soluble in organic solvents.

The following examples will serve to illustrate my invention:-

Example 1 To 39 parts by weight of -ethyl-flropylacrolein dissolved in volumes of nzene 21 parts by wei ht of aniline in 25 volumes of benzene are a ded, whereupon heating is effected under reflux on the water bath for from 3 to 4 hours. In the course of the re- Example 2 200 parts by weight of aniline are mixed with 200 parts by weight of crude a-ethylg-propyl-acrolein (as obtained from normal utyl aldehyde by stirring with dilute caustic soda lye until the whole of the but 1 aldehyde has disappeared). Owing to t e reaction the mixture becomes heated and after some minutes water separates out. The product is then heated for from 1 to 2 hours first on a water bath and subsequently on an oil bath to 140 C. after which the excess of aniline is removed in a vacuum at 145 0., an oily residue remaining Gaul HO OH=N IE7 60H; Example 3 150 parts by weight of a-isopropyl-/3-isob'utyl-acrolein are mixed with 120 parts by weight of aniline, 50 parts by wei ht of anhydrous zinc chloride are adde and the whole is heated on a water bath for several hours. The zinc chloride is then removed by extraction with water and the remaining 011, if desired after solution in benzene is heated in a vacuum for several hours at 140 C. Instead of zinc chloride other condensing agents may be em loyed. The product has most probably the ormula:

I claim 1. The process which comprises causing an alpha'beta-di-alkyl-substituted acrolein to react with a primary aromatic amine in the presence of an inert solvent and an agent capable of exertin a condensing action.

2. A process or the manufacture of condensation products from an alpha-beta-dialkyl-substituted acrolein with a primary aromatic amino consisting in the interaction of these components in the presence of a condensation 9. nt at a temperature between about 80 and about 140 C.

3. The process which comprises causin u-ethyl-B-propyl-acrolein to react upon an1 line at a temperature between about 80 C. and about 140 C.

4. As a new roduct the compound of the probable form a:

being an oily substance, diflicultly soluble in water, soluble in organic solvents and being valuable accelerators in the vulcanization of rubber.

5. The process' which comprises causing alpha-ethyl-beta-prop'l-acrolein to react upon a primary aromatic amine.

6. As new products, the compounds of the general formula:

wherein R stands for an aromatic nucleus, being generally oils diflicultly soluble in water, soluble inorganic solvents and being valuable accelerators in the vulcanization of rubber.

In testimony whereof I have hereunto set my hand.

WALTER KROPP.

4. As a new roduct the compound of the probable form a:

nc===-o-on=N (51H: (JaHl wherein R stands for an aromatic nucleus,

being generally oils diflicultly soluble in water, soluble in organic solvents and being valuable accelerators in the vulcanization of rubber.

In testimony whereof I have hereunto set my hand. WALTER ROPP.

P I SO LAI M E R 1 ,845,755.-Walter Kropp, Elbe Held, near Cologne-on-the-Rhine, Germany. NEW Aononnm CONDENSATIQN Paonuc'r. Patent dated February 16, 1932. Disclaimer filed June 22, 1934, by the assignee, I. G. Farben'industrie Aktiengesellschafl. Therefore, enters this disclaimer tocert in of th 1 patent, nqmel claims 4 5 and 6' a. e c aims of the above Identified zette July 24, 1934.]

DISCLAIMER 1,845,755.Walter Kropp, Elbe Held, near Colo e-on-the-Rhine, Germany. NEW AcRoLEIN CONDENSA'IION PRODUCT. atent dated February 16, 1932. Disclaimer filed June 22, 1934, by the assignee, I. G. Farbenimiustrie Aktz'engesellschafl.

Therefore, enters this disclaimer to certain of the claims of the above identified patent, nemel claims 4, 5 and 6. 

